Top 20 Greatest Comedy Musicians

Although he started out as a game show writer and producer, it was through his hilarious song parodies that Allan Sherman played his way into our hearts. Topping the charts in the early 1960s with a trio of comedy albums, Sherman bagged a Grammy nomination for Album of the Year for his first album, “My Son, the Folk Singer.” His third effort featured the hit single, “Hello Muddah, Hello Fadduh” about the horrible experiences of a boy at summer camp, set to a jaunty classical tune. Sherman inspired a generation of song parodists and is even responsible for a classic “Simpsons” joke.

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#19: Marc Rebillet

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Now THIS is improv. Originally from Dallas, Texas, this highly-skilled electronic comedy musician built up a fanbase with his improvised — and hilarious — jams, and went viral with scantily-clad videos of him improvising songs in his apartment. With musical styles ranging from groovy R&B tunes to straight-up dance jams laced with his vulgar sense of humor, Rebillet has toured the world with just his loop station, keyboard and aggressively sensual vocals. His songs are witty enough to crack you up, but still so funky that they stay on repeat in your head. They don’t call him the Loop Daddy for nothing.

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#18: Nice Peter & EpicLLOYD

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Who said history lessons can’t be fun? Peter "Nice Peter" Shukoff and Lloyd "EpicLLOYD" Ahlquist burst onto the scene in 2010 after creating the YouTube series, “Epic Rap Battles of History.” Featuring historical and pop culture figures going up against each other, MC-battle style, the series became wildly popular for its dead-on impersonations, hilarious disses and surprising celebrity appearances. With unforgettable battles like “Adolf Hitler vs. Darth Vader,” “Donald Trump vs. Hillary Clinton,” and even a battle between each other, these guys bring together entertainment and education to make a truly epic combo. Both men also make solo comedy music and have taken their show on the road multiple times.

A legend in the musical comedy genre, Reggie Watts ups the ante with his exceptional beatboxing skills. Armed with only a keyboard, looping machine and his formidable voice, Watts’s live performances are 100% improvised and typically feature him singing, rapping and beatboxing his way through the most random train of thoughts. Nevertheless, his sets remain coherent, nuanced and funny as hell. His inventive talent has taken him from concerts to being the bandleader on “The Late Late Show with James Corden.” With a style that’s every bit as puzzling as it is entertaining, Watts has proven himself to be a truly indescribable genius.

Rachel Bloom is the bomb. And she has the gift of making you think, “Well, that escalated quickly.” Bloom got her first jolt of fame when her sexually explicit song about science fiction writer Ray Bradbury went viral in 2010. She followed up with more comedy music videos and an album three years later. Her cult CW series, “Crazy Ex-Girlfriend,” premiered to critical acclaim and featured multiple original comedy songs every episode. Bloom frequently takes on taboo topics and provides spot-on social critique, making us laugh and cringe at the same time.

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#15: Spike Jones

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Here’s an old-school entry with real chops.This satirical musician from Long Beach, California began his career in the 1930s as a band percussionist, frequently playing in orchestras and on radio shows. He quickly got bored with these routines and decided to shake things up by making parodies and novelty songs. With his band, the City Slickers, Jones spoofed popular songs by injecting outlandish sound effects like gunshots, whistles, and other bizarre musical instruments, elevating their music above mere comical lyrics. Nowhere is this better used than in their hit version of the romantic ballad, “Cocktails for Two,” which takes the beloved croon down a path of absolute comedic chaos.

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#14: Tom Lehrer

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If there were ever a Mount Rushmore of musical comedy, Tom Lehrer’s face would certainly grace it. Starting in the 1950s, Lehrer developed a cult following for his satirical songs about controversial subjects. Deemed problematic, radio stations refused to air his music, resulting in their very slow, yet steady spread in popularity. Lehrer’s songs got significantly more political as the ‘60s rolled around, tackling topical issues like racism and nuclear warfare. His biting satire and twisted sense of humour, coupled with his love for math and science, set him apart from other satirists of his time and cemented him as one of the founding fathers of comedy music.

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#13: Ray Stevens

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Well, giddy up! ‘Coz this country cowboy’s got more than just a few jokes. With a career spanning over sixty years, novelty country singer Ray Stevens has proven to be the musical renaissance man, taking on producing, publishing and songwriting roles over the years. His music features the perfect blend of comedy and country, poking fun at various aspects of pop culture and religion. Brandishing his wacky humor and sometimes beloved, sometimes obnoxious catalog of voices, Stevens put novelty songs on the charts and received two Grammy nominations for Best Comedy Recording. Even after such a long time, as of 2021, Ray Stevens is doing his thang!

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#12: Tim Minchin

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He’s a musician at heart, but his sounds are steeped in comedic satire. Born in England and raised in Western Australia, Tim Minchin has the appearance of a red-haired Edward Scissorhands, and his pronounced atheism cuts through each and every performance. He’s a self-aware composer of cabaret spectacles, and sometimes has a complete orchestra accompanying his sharp social commentary. While Minchin never actually attended a comedy show before the start of his career, watching him on stage you just know how blessed he is with comedic talent.

In a world saturated with male comedy musicians, this impressive duo brings a much needed female perspective to the scene. Riki Lindhome and Kate Micucci answer the question, “What if Joni Mitchell sang explicitly about sex?” Their easy-on-the-ear folk music provides a rather unusual contrast to the raunchy, no-holds-barred subject matter. This crude sense of humor helped them land their own show on IFC, detailing their attempt to make it big in Hollywood. Whether they’re strumming their guitars to lyrics about God’s loophole to virginity or ranting about pregnant women, Garfunkel and Oates have never been afraid to sing what we’re all thinking.

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#10: Frank Zappa

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Does humor belong in music? This rock legend definitely thought so. At heart, Frank Zappa was an innovative composer and songwriter whose zany sense of humor was only secondary to his one-of-a-kind musical virtuosity. Having taught himself to play the drums and guitar, Zappa went on to create a diverse body of work, blending his sharp social commentary on American culture with raunchy humour and amazing musicianship. He blended all his musical talents to make timeless masterpieces, as funny as they are thought-provoking and complex. Constantly treading a fine line between satire and offensiveness, it may take you a few listens to really pick up what Frank Zappa’s putting down.

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#9: Stephen Lynch

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This Michigander musician in stand-up comic’s clothing doesn’t need much to crack you up. Hand him a guitar, put him on a stage, and he’s good to go. Stephen Lynch pushes the boundaries of comedy by satirizing the banality of everyday life over his soft and sincere melodies. His songs typically start off calm and innocent, with Lynch belting out lyrics about a mundane topic, before taking bizarre turns that only get more absurd as the songs progress. The juxtaposition between his wildly provocative material and his earnest guitar strumming, coupled with his theatrical stage presence, makes Lynch’s sets way more hilarious than you’d ever expect.

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#8: Lil Dicky

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He’s either the most hilarious rapper in America, or the baddest MC to ever do comedy. Like a lot of entries on this list, Lil Dicky got his start on YouTube when the music video for his song, “Ex-Boyfriend” went viral in 2013. Two years and an aggressive Kickstarter campaign later, Lil Dicky released his debut album, “Professional Rapper,” which went to number one on the comedy charts. His musical range is unquestionable, going from spitting rapid-fire rhymes against Snoop Dogg to belting power ballads with Brendon Urie, while maintaining his profane sense of humor. Not one to be confined, Dicky even became a TV star, playing a fictionalized version of himself on his FXX comedy series, “Dave.”

This awesome New Zealand duo — or, as they have described themselves, "New Zealand's fourth most popular guitar-based digi-bongo acapella-rap-funk-comedy folk duo," held down their own TV series from 2007 to 2009. Bret McKenzie and Jemaine Clement originally formed a group in 1998 when they were college roommates, and by 2004, their polished act allowed them to heavily improvise on their own BBC2 radio series, which ultimately paved the way for their American mockumentary experience. While “Flight of the Conchords” doesn’t often perform these days, due to the duo’s many other projects, they did reunite for a great HBO special in 2018.

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#6: Ninja Sex Party

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If you hear the name of this band and find yourself whispering “yes, please,” well then you’ll probably enjoy their brand of synth pop comedy. Composed of Danny Sexbang and Ninja Brian, these goofballs offer up sex advice while making you fall over from laughing so hard. Sure, you may not find them lighting up the stage at Carnegie Hall, but you can expect them to help you take control of your sex life courtesy of hilarious music videos and astonishingly profound lyrics. Or if video games are more your thing, then give their side project Starbomb a shot.

They are the chosen ones, and in 2006, they gave us “The Pick of Destiny”. With Kyle Gass plucking’ away on the guitar and Hollywood star Jack Black offering his own style of heightened theatrics, Tenacious D leans more toward the epic than ironic, sophomoric stunts. These guys know they are superstars, and their big-boy performances took them all the way to the American Music Awards. They first made a name for themselves by appearing in various late
‘90s films, and by the dawn of a new decade, they were the wonder boys of HBO.

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#4: Bo Burnham

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Bo really can do it all. Burnham rose to fame in 2006 after his family-unfriendly home videos went viral. He later signed a deal with Comedy Central Records and at seventeen became the youngest person to film a comedy special for the channel. His music takes a satirical, and often controversial, approach to difficult subjects such as race, gender, sex and religion. Burnham wears a variety of hats, having directed two comedy specials and his debut feature film, “Eighth Grade.” In 2021, he returned to his roots with his homemade special, “Bo Burnham: Inside,” using meta humor to address his mental health during the COVID-19 pandemic.

The most pretentious of rock stars are unlikely to find any humor in this fictional rock band, and most probably thought the 1984 feature film was actually about them. Rob Reiner’s satirical take on musicians and the filmmakers who cover them not only earned a cult following, but is notable for its heavy improvisation. The band’s lineup consisted of Michael McKean, Christopher Guest and Harry Shearer, all of whom slayed in their roles, leading many to believe their faux rock unit was a real thing. And in the scope of iconic films and comedy musicians, they certainly are the real deal.

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#2: The Lonely Island

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This absurdist comedy trio from Berkeley, California gained immense popularity after being hired by “Saturday Night Live” in 2005. With Akiva Schaffer and Jorma Taccone as writers and Andy Samberg as a writer and performer, The Lonely Island quickly came to the forefront of the sketch show with their hilarious spoofs of rap music and hip-hop tropes. Their fancy, star-studded music videos helped revitalize “SNL” and cultivated an online relevance for the long-running show. Their wacky sense of humor persists on all four of their studio albums, work which earned them a Grammy nomination for Best Comedy Album. The Lonely Island keeps sailing on, which makes sense, since “ WE’RE ON A BOAT!”

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#1: “Weird Al” Yankovic

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He’s the Godfather of musical satire and the President of Pop Culture Parodies. Originally touted by Dr. Demento, a teenaged Al Yankovic offered his own take on The Knack’s “My Sharona” in 1979, which led to his first record deal. It’s not that he boasts a beautiful voice or leading man looks, it’s that he’s always working and knows how to hit the right chords with mainstream audiences. Even in the internet age, Weird Al still knows how to stay relevant with new generations of devoted fans. Keep on rockin’, Weird Al!